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$69+ Cheap flights from Midway (MDW) to Pittsburgh (PIT)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PIT
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
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Cheap flight deals from Midway to Pittsburgh

Cheapest flights from Midway to Pittsburgh
Explore the most affordable flight options available from Midway to Pittsburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.

This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:36 pm
MDW
-
PIT
1 stop3h 02m
Delta
Tue 6/24:45 pm
PIT
-
MDW
1 stop5h 24m
Delta
Deal found 5/5$177
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:10 am
MDW
-
PIT
2 stops6h 45m
Southwest
Thu 6/48:15 pm
PIT
-
MDW
1 stop3h 45m
Southwest
Deal found 5/5$182
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:30 am
MDW
-
PIT
1 stop5h 45m
Southwest
Mon 6/18:00 pm
PIT
-
MDW
Nonstop1h 30m
Southwest
Deal found 5/4$187
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:40 pm
MDW
-
PIT
1 stop3h 35m
Southwest
Wed 5/276:25 am
PIT
-
MDW
2 stops9h 30m
Southwest
Deal found 5/4$188
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3012:45 pm
MDW
-
PIT
2 stops9h 20m
Southwest
Sat 6/67:05 pm
PIT
-
MDW
Nonstop1h 30m
Southwest
Deal found 5/4$192
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:36 pm
MDW
-
PIT
1 stop3h 02m
Delta
Mon 6/14:45 pm
PIT
-
MDW
1 stop5h 24m
Delta
Deal found 5/4$197
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:40 am
MDW
-
PIT
2 stops8h 55m
Southwest
Sat 8/224:40 pm
PIT
-
MDW
Nonstop1h 25m
Southwest
Deal found 5/5$227

Find flight deals from Midway to Pittsburgh

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Pittsburgh (PIT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(Delta)

One-way from

$69
(Southwest)

Popular in

March

Cheapest in

September

Average price

$533

Good round-trip deal

$343 or less

Good one-way deal

$115 or less
Provider with most accurate pricing for Chicago Midway-Pittsburgh flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Pittsburgh flights.
Search Deals
From Chicago Midway to Pittsburgh
Search Deals
One-way flight from Chicago Midway to Pittsburgh
Search Deals
Highest demand for flights based on searches. 35% potential increase in price ($182 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Pittsburgh.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Pittsburgh.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Pittsburgh that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Pittsburgh that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 5/28

7:50 am-12:55 pm

1 stop4h 05m

Pittsburgh

Thu 6/4

8:10 pm-8:40 pm

Nonstop1h 30m

$187
Quickest round-trip

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 5/28

7:40 am-10:00 am

Nonstop1h 20m

Pittsburgh

Mon 6/1

1:35 pm-2:05 pm

Nonstop1h 30m

$212

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Mon 6/8

5:05 pm-11:05 pm

1 stop5h 00m

Pittsburgh

Sat 6/13

5:50 am-1:10 pm

2 stops8h 20m

$285

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 5/27

7:50 am-10:15 am

Nonstop1h 25m

Pittsburgh

Sun 5/31

6:10 am-1:05 pm

2 stops7h 55m

$286

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Tue 5/26

10:10 am-5:55 pm

2 stops6h 45m

Pittsburgh

Fri 5/29

5:45 am-1:10 pm

2 stops8h 25m

$326

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Mon 6/15

6:50 pm-9:15 pm

Nonstop1h 25m

Pittsburgh

Mon 6/22

8:10 pm-8:40 pm

Nonstop1h 30m

$343

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 7/11

7:45 am-10:15 am

Nonstop1h 30m

Pittsburgh

Sat 7/11

7:05 pm-7:35 pm

Nonstop1h 30m

$343

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 6/12

1:35 pm-4:00 pm

Nonstop1h 25m

Pittsburgh

Sun 6/14

7:50 pm-8:20 pm

Nonstop1h 30m

$354

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Fri 6/5

1:35 pm-4:00 pm

Nonstop1h 25m

Pittsburgh

Sun 6/7

7:50 pm-8:20 pm

Nonstop1h 30m

$354

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Thu 6/25

12:20 pm-10:35 pm

2 stops9h 15m

Pittsburgh

Sat 6/27

7:05 pm-7:35 pm

Nonstop1h 30m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Midway to Pittsburgh

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Pittsburgh in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Pittsburgh flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Pittsburgh flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Pittsburgh flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Pittsburgh flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Pittsburgh flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Pittsburgh

Have a flexible travel schedule? Discover the best time to fly to Pittsburgh from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Pittsburgh

What is the cheapest time of day to fly from MDW to PIT?

Find hourly flight availability from Midway to Pittsburgh. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 6, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 19% on flights from Chicago Midway Airport to Pittsburgh by exploring options for tickets in the afternoon.

How much does it cost to fly round-trip from Chicago Midway Airport to Pittsburgh?

The best insider tips for Chicago Midway Airport to Pittsburgh flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Pittsburgh trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
John Walton

John Walton

Expert on PIT

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more

Reviews of airlines servicing Pittsburgh

Get insights into the airlines that provide service to Pittsburgh. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Pittsburgh. Reviews last updated May 6, 2026.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to Pittsburgh. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,305 reviews

Entertainment

7.5

Comfort

8.0

Overall

7.9

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,305 reviews
Southwest
7.9
Good
4,305 reviews

Entertainment

7.5

Comfort

8.0

Overall

7.9

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Midway to Pittsburgh. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Pittsburgh from Chicago Midway?

    Pittsburgh (PIT), located 13.5 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Pittsburgh. 1 airline have flights to Pittsburgh from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Pittsburgh should not be difficult; the airport handles an average of 2 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Pittsburgh?

    Airlines like Southwest fly from Chicago Midway Airport to Pittsburgh in about 4h 05m. The time it takes to get you to your destination can typically vary by up to . The distance from Chicago Midway Airport to Pittsburgh is about 400 mi.

  • What is the cheapest airline to fly from Chicago Midway Airport to Pittsburgh round-trip?

    Currently priced at $116, Southwest will fly you from Chicago Midway Airport to Pittsburgh and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Southwest is currently priced 65% below the average price you’ll pay for this route.

  • What are the cheapest flights from Chicago Midway Airport to Pittsburgh?

    While on average a flight from Chicago Midway Airport to Pittsburgh is generally $363, our data shows the cheapest flight currently is $68. When looking at the most popular route, (Chicago Midway - Pittsburgh), you can expect to pay $137 for that flight.

  • Can I find deals for flights from Midway to Pittsburgh that include hotel bookings?

    Yes. In addition to deals on Midway to Pittsburgh flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Pittsburgh?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Pittsburgh.

  • Can I find deals for business class flights from Midway to Pittsburgh?

    Yes. Cheapflights offers flight deals from Midway to Pittsburgh by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Pittsburgh?

Book flights to Pittsburgh if you plan to visit one of these locations
Mars
Chester
Steubenville
Washington
Monroeville
Wexford
Belle Vernon

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Midway to Pittsburgh

Discover the top airline that operate flights from Midway to Pittsburgh. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$116Average$354FlexibilityNo cancel feeOn-time63%

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